New amino-1.1&#39;-anthrimidcarbazols



Patented June 9, 1931 UNITED STATES WALTER MIEG, OF OPLADEN, AND FRITZ BAUMANN, OF LEVERKUSEN-ON'-TI-IE-RHINE, GERMANY, ASSIGNORS TO GENERAL ANILINE WORKS, INC 02 YORK, Y., A

' CORPORATION OF DELAWARE" NEW AMINO-51.1HANTHRIMIDOAREBAZOLS a No Drawing,

The present invention relates to new amino-1.l-anthrimidcarbazols. 7 We have found that when reacting with strong sulfuric acid upon a-acylamino-LY- 5 anthrimidcarbazols of the probable general formula:

wherein at least one stands for an acylamino residue, w stands for a hydrogen atom, which may be replaced by an acylamino group, the

corresponding a-aminoanthrimidcarbazols heretofore unknown are obtainable, which 7 2.3 may be used as vat dyestuffs or as intermediate products for the manufacture of dyestuffs. We prefer to execute the saponification by means of a sulfuric acid of about 60 to 66 B. and at temperatures ranging from 10 about 60 to 120 0. mainly depending on the strength of the sulfuric acid and. on the kind of the starting material applied. When saponifying by means of a sulfuric acidof about 60 B. the amino-.anthrimidca'rbazols separate during the reaction as sulfates and may be isolated in the usual manner. When working with a stronger sulfur'ic'acid it will be advantageous to dilute the same after the saponification until the corresponding sul-' .4 fates separate. Obviously the working up of Application fil'ed March, 15, 1 928. Seria1:No. 2'82,04=0.

soluble in strong sulfuric acid with brown to olive colorations, dyeing cotton from the hy drosullite vat'brown'to 'corinthshades. r

"The following examples illustrate our'l in vention without limiting it thereto: i i

Example 1. 6parts-by weight of 4-ben- 'FFICE",

zoyl-amino-1.1-anthrimidcarbazolare heated in pars by volumeof sulfuric acid of 96% strength to 95 C. until samples diluted with water no more'change in color. 'Now the reaction mixture is diluted by means of 20 parts by volume of {a sulfuric acid of 50% strength whereby the sulfate of the l-aminol.l-anthrimidcarbazol deposits which is filteredand"Washed first with sulfuric acid of B. and'the n with water. The t-aminol.l-anthrimidcarbazol having the probable is thus obtained in form of a dark grey pow-. 1

der, which dissolves in sulfuric acid of 96% strength and in hot nitrobenzene with a brown coloration. The alkaline hydrosulfite vat of the product is yellowish brown.

benzoyldiaminol.lfianthrimidcarbazol are,

heated in; 150 vparts by. volume of a sulfuric acid OfGO FB. for aboutone hour at 120 C whilestirring. When cooled the sulfateof the 5 .5-d iamino-l.1 anthrimi'dcarbazol separates, which is further treated as mentioned in Example 1.

The 5.5-diamino-1.1'-anthrimidcarbazol of the probable formula:

forms .a red-brown powder, soluble in strong sulfuric acid with an olive brown coloration which changes to blue at the addition of formaldehyde. It is difiiculty soluble in the usual organic solvents and crystallizes from much nitrobenzene in finered needless. It

dyes cotton from an orange-yellow hydrosulfite vat strong reddish-brown shades.

When using instead of a sulfuric .acid of 60 B. a sulfuric acid of 96% strength saponification takes place already at a temperature of 60 C. I

Example 3.1 part by weight of 4.5-d-iacetyldiamino 1.1-anthrimidcarbazol are heated in 20'parts by weight of a sulfuric acid of 96% strength to 80 C. until samples, poured into water no more change in color. The 4.5-diaminoanthrimidcarbazol, isolated in the usual manner, forms a violet brown powder, soluble in strong sulfuric acid with a pale reddish brown coloration, difliculty soluble in the usual organic solvents. cotton from the alkaline hydrosulfite vat corinth shades.

We claim:

1. Compounds of the probable general formula:

wherein at least one 3 stands for an amino group, w stands for a hydrogen atom, which may be replaced by an amino group, said products being yellowish brown to dark grey powders soluble in strong sulfuricf acid with brown to olive colorations; dyeing cotton fromthe hydrosulfite vat brown to corinth shades.

2. The compound of the probable formula:

1 der, soluble in strong sulfuric acid with an olive-brown coloration which changes to blue at the addition of formaldehyde, dyeing cotton from the hydrosulfite vat strong reddish brown shades.

In testimony whereof we have hereunto set our hands. I

' WVALTERMIEG.

FRITZ BAUMANN.

It dyes 

